MR. SHUHENG XU

SuFExable Isocyanides for Ugi Reaction: Facile Synthesis of Sulfonyl Fluoro Peptides

The sulfur(VI) fluoride exchange (SuFEx) reaction has become a good click chemistry transformation and acted as a powerful tool in medicinal chemistry and materials science. Therefore, the investigation of versatile SuFExable synthon and SuFEx compatible reactions is highly desirable. Herein, the sulfonyl fluoro isocyanides were first developed as a new type of SuFExable synthon, and used as flexible building blocks in the Ugi four-component reaction (U-4CR). Hence, the preparation methods of differential SuFExable isocyanides were established, including both aryl and alkyl sulfonyl fluoro isocyanides. The sulfonyl fluoro tolerable Ugi reaction was established and the substrate scope was investigated, and various sulfonyl fluoro α-amino amides and peptides could be reached in a one-step synthesis. Therefore, this protocol opens a new vision for SuFExable building block and click chemistry, and also provides a distinct approach to sulfonyl fluoro peptides.